Maggies Dark Side
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Maggie's Punishment, Chapter 1 free porn video
I have known Maggie Anderson for several years now and we regularly see each other. We aren’t committed to each other in any way, but we both enjoy each other’s company and see a lot of one another. I understand her and she apparently gets what she needs from me.
Maggie has had a troubled past and it has led to some very unusual needs for her. As a child, she had less than ideal parents–her mother was a bitter, cruel, and heartless woman who blamed her for all the trouble she had and for ruining what she imagined her life should have been like.
Maggie's mother was abusive both in word and deed, never giving Maggie any kind of praise or credit for doing anything right and always belittling and degrading her. She slapped her and punished her severely for the slightest infraction.
Maggie’s father was no better; a spineless pussy of a man who wouldn’t go up against his wife no matter what she did. He would rather stay away from the house, working or out at the bars, than go home to face his bitch of a wife. When he did come home, he was drunk and he, too, treated Maggie cruelly.
Maggie’s callous and brutal childhood caused her to have very low self-esteem and she always thought that she was more trouble than she was worth and wondered why any man would put up with her. Consequently, she didn’t date (not that she could–her mother would pounce on her and call her a whore if she even smiled at a boy!) and so she never knew what it meant to be loved.
Maggie lived her sad life not knowing what it was like to be cared for not knowing her own worth until she was twenty-six years old. That’s when I met her. She was working as a waitress in a small-time cafe; a job that was far beneath her and which did nothing to raise her opinion of her self-worth.
I had just taken a job with a large company whose office was just down the street a couple of blocks and I stopped into her cafe for lunch one day. She waited on me that day and I saw something in her eyes when she looked at me. She was very shy and didn’t speak much except to take my order.
When she brought my food I asked her what days she usually worked. They coincided pretty much with the days I was at the office so I decided to make this cafe a regular lunch thing and see if I could get this shy, reserved woman to open up a little.
Slowly over the next three months or so she began to relax when talking to me and I could see the walls slowly crumbling. I had even got her to sit with me when she took her breaks and we could talk a bit.
One day I was in the cafe for my regular lunch break when Maggie came to take my order. I ordered the special as usual and as I finished Maggie came back to give me the check. This time, though as she began to walk away I grabbed her wrist to stop her.
"Maggie, go out with me this weekend. We could go to a movie, to dinner, or whatever you’d like,” I said. Maggie looked at me, stunned like I had just walked into the cafe naked with a clown’s multicolored wig on!
“You want to go out with me?” she said.
“Yeah if you’d like to–unless you have a boyfriend or something,” I said.
“No, I don’t have a boyfriend. But why me?” she asked. This was my first hint of Maggie’s self-esteem issues.
“Well I have been coming in here for a while now, and I always ask for you. I thought maybe we could get to know each other a little so we would have more to talk about when I come to see you than the weather or the daily special here,” I said, smiling.
“I don’t know…” she said looking around. I think she was looking for a reason to rush off. I had to move quickly and seal the deal.
“Aw c'mon Maggie. Look, I like coming here and I like talking to you. I would just like to get to know my favorite waitress is all. Please say you’ll go out with me,” I said.
She thought about it for a bit. “Okay, I’ll go out with you. Dinner sounds nice,” she said looking down and fiddling with her hands nervously.
We decided that weekend we would go out. Saturday evening I drove to the address she gave me. It turned out to be a small trailer court and as I drove past the rows of trailers I noticed that almost all of them were older and in rather well-used condition.
Frankly, some of them barely passed as living quarters! I drove on looking at some of the depressing conditions of some of the trailers until I got to the end of the row. There sitting by itself (the lot next to it was vacant) was Maggie’s trailer.
Maggie’s trailer was a small 14’ x 60’ built back in the early ’70s. It had two bedrooms (well one bedroom and one very small room that could work as a child’s room in a pinch). It, too, was in dire need of work, although she had made some attempts to decorate the yard with some garden pieces and there were curtains on the windows.
But I could tell this place was haggard and time-worn. I put it out of my mind and concentrated on the girl inside. I walked up her old wooden walkway and knocked on her door.
“Hi John, come on in I’m just about ready,” she said as she opened the door. I opened the screen door and went inside. The inside of the place was sparsely decorated with a hodgepodge assortment of second-hand store furniture and accessories. I could tell that very few things in her small trailer were for ornamentation alone–most everything had a purpose. There simply wasn’t room in her small trailer or her life for fancy frills.
“Did you have any trouble finding my place?” she asked.
“No, no problem,” I said.
“That’s good. Well, give me a minute and I will be ready,” she said. As I sat on the old worn love seat in her living room, she went back to the bedroom to finish getting dressed. She came back out after about five minutes.
“I’m ready now, John. I hope this is okay… I don’t go out much, really, and you never said where we were going to eat,” she said. Her deportment was one of apprehension and embarrassment. She was ashamed of her trailer and her station in life.
“You look fine, Maggie. I thought we would go to Barron’s. Their steaks are really hard to beat!” I told her. She smiled and we left for the restaurant.
After a nice dinner and conversation, we headed back to her trailer. I was sensing that she was nervous about how the good night would go–whether to invite me in or not and what would happen either way. Maggie knew that I was a businessman and I would come into the cafe in a suit. She was a waitress and not even the head waitress. She didn’t feel she had much to offer.
Inevitably the moment of truth came and I walked her up her walkway to her door. She stood there trembling, still not knowing what to do next. But I knew what to do. Knowing this was our first date, and wanting to see her again, I let her off easy.
“I had a wonderful time tonight. I’m glad you decided to go out with me. And I’d really like to see you again,” I said.
“Y-you would?” she said. “John you know that I…” she let her words trail off. I knew what she meant.
“Maggie, sweetheart, I don’t care that you are a waitress. I don’t care that you live here, I don’t care about any of that. I enjoy your company and I like being with you. And you are very pretty when you dress up. So don’t worry about any of that stuff. You have a lot to offer and I’m interested, okay?” I said.
We kissed there at her door and I let her get inside before I turned and went home myself. As I turned to get in my car, I saw her peeking out through the curtain of her trailer window. I waved goodbye and saw the curtain suddenly close–I had caught her watching me. I smiled and left for home.
We went out four more times after that, each time I picked her up and dropped her off. I made no moves to try anything with her; as shy and reserved as she was, I didn’t want to move too fast and scare her off. I figured that as long as we were dating, she would let me know when the time was right.
On our fifth date we had gone to the movies–some sappy romantic love story she wanted to see–and then to a restaurant for a little dinner. It was at the restaurant that I learned a lot more about my Maggie.
“John, I need to tell you some things about me. You and I have been seeing each other now for a while and I want to let you know what you are getting yourself into before we go much further. I really like you John and I don’t want to keep anything from you,” she said.
“Okay, this sounds serious. So tell me about Maggie,” I said, putting down my fork and listening intently.
That’s when Maggie told me about her past, about her childhood, and about the past wrongs that were done to her. She explained that because of all that had happened, she had a very low opinion of herself. “I started seeing a counselor for it, but it got too expensive for me to continue. He wasn’t really helping anyway,” she explained.
She went on to tell me that she’d had been interested in a couple of guys before and tried dating them, but when they found out what she needed, they couldn’t deal with it and it ended about as quickly as it began.
“What is it you need, Maggie? What is so hard about dating you?” I asked.
“Well, I'm pretty messed up John. I’m almost afraid to tell you, but you’d find out soon anyway, so here goes. Because of what has happened to me, I need to be… well, I need to be treated badly in order to feel loved. Does that make any sense to you?
"The only way I knew my parents even recognized my existence was when I was being yelled at, slapped, or abused. I don’t remember having a civil conversation with my parents about anything. So when a guy comes along, like you, and treats me like I’m special, I can’t handle it.
"I don’t know what to do with all those sweet, nice things you say, or when you open the door or pull out a chair for me. But slap me across the face, call me nothing but a cheap whore, or throw me on the bed and fuck me like I’m just a hole for your cock and I can relate. Sorry if it sounds bad–it is–but that’s the life I have known,” she said.
“So you like it when a guy mistreats you, calls you a slut and a whore, and degrades you?” I asked.
“Yes. Not only do I like it, but I also need it. It’s the only way I can get aroused and get turned on. I can’t understand the concept of "making love” like you see in the movies. That has never happened to me. It would be like you trying to understand what it feels like to be a woman and have a man inside you. You have no frame of reference,“ she said.
"Well, Maggie, believe it or not, what you have told me makes sense in a weird way. I could tell right off that there was something different about you. Not different in a bad way, just different in an ‘I gotta find out what this girl is about’ way. Your meek and humble, almost mouse-like attitude had me curious.
"And now that you explained it, it makes sense. And no, I’m not scared off–just the opposite, actually. I want to continue seeing you, and if being mishandled is what you need to feel that I care for you, then I’m willing to give it a try.
"But I also have to tell you that while I am treating you like the whore you want to feel like, I will also be working to get you to understand just what a special person you really are. I will slap you around and fuck you like I am trying to break you, but afterward, I will cuddle you and make you feel safe in my arms.
"I want to make you understand that you do matter–you matter to me and you matter to yourself. And unlike that counselor, you can afford my services! Deal?”
“That sounds wonderful, John. Yes, it’s a deal!” she said smiling.
We finished dinner and went back to her place. This time, she invited me in and I accepted. we went in and sat on the love seat and she explained more about the things she liked and needed and what got her hot.
I paid close attention, this was a little new to me and I wanted to be able to give Maggie whatever it was that made her feel loved and what she needed to get off. Despite mistreating her, I still wanted her to cum and get the release she wanted.
“One thing that really makes me hot is the whole punishment thing. I love to pretend I did something wrong and need to be punished. And then you yell at me, tell me how worthless I am and how you are tired of telling me not to do what I did and then punishing me. And remember don’t be easy on me either–I need to really feel the pain, I need to feel like this is real in order to orgasm,” she said.
“Punishment eh? Okay, but if I’m punishing you does that make me ‘Daddy’ or do you want to me to be your ‘Master’ or ‘Sir’, Maggie?” I asked.
“Well 'Daddy’ wouldn’t work–most Daddy’s love their little girls. And Master makes me sound like a slave, not a whore. So I guess Sir would be the best,” she said.
“Okay, from now on when we are together alone, I am Sir,” I said.
“Yes Sir,” she said, smiling. And so our new relationship was formed. Over the next few weeks we met every weekend and began working together under these new roles; me as Sir and her as the naughty little whore that always got in trouble and needed to be punished.
I tried to be the “Sir” she needed me to be and she helped me to see what that meant. I was surprised at the intensity her–kink, I guess is the best way to describe it–took. She played her role completely and she wanted me to as well. And when she told me she wanted to be punished she wasn’t joking–it seemed like the more I gave her the more she wanted.
We started out with me giving her OTK (over the knee) spankings with my bare hand, then we moved to hairbrush spankings. When that no longer worked for her, I picked up a wooden spoon, then a ping pong paddle and used them. Still, she needed more.
We were meeting every Friday or Saturday for our playtimes. With the cafe being downtown in the business district, weekends were slow times and Maggie had Saturday and Sundays off. If Fridays weren’t too hectic for either of us, we would meet Friday night; if not we had Saturday to get together.
This schedule worked well for us, I could meet with Maggie, give her whatever punishment she “needed” for her imagined wrongdoings, and she would be in good shape for work on Monday mornings.
We established a pact of sorts; whatever I did to her, I was not to leave any marks that could be seen at work. If I slapped her face, I would do it so as not to give her a busted lip or black eye. Only a red mark on her cheek that would go away before work on Monday.
Of course, her ass, legs, and the rest of her was fair game–she could hide the welts and bruises under her clothes. She might walk funny, but she could pass that off as sore from exercising or some weekend activity.
One week she told me at lunch on Friday that she wouldn’t be able to get together that weekend; one of the other waitresses was out sick and she was going to pull a couple of extra shifts for some much-needed overtime. This was fine with me–it gave me a chance to prepare a little more for the next weekend when we would get together.
Since we started seeing each other I had tried to give Maggie what she wanted and needed. I had tried to be the “Sir” she desired me to be.
But that wasn’t me–I wasn’t really comfortable being that degrading, that mean, and that abusive. I had always treated women with respect and care. Oh sure, from time to time I would call her a slut or spank her ass playfully, and I have made her crawl and things like that. But nothing even close to the degree Maggie was looking for from me.
However, I was really falling for this shy introverted woman and I wanted to be all that she wanted. I knew the reasons why she was the way she was and at first, I’ll admit, I felt sorry for her. I mean no one should grow up under those conditions. But Maggie didn’t want my pity. I had to respect her for surviving her past and for wanting to rise above it.
So I was determined to be a proper Sir and when the next weekend came I was ready…
Alma
- 21.02.2021
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- Spanking
